Method of killing yeast or fungi with dihydrocarvone

ABSTRACT

A method of killing yeast or fungi which comprises treating the yeast or fungi with a toxic amount of dihydrocarvone.

TECHNICAL FIELD

The object of this invention is to demonstrate a method of using dihydrocarvone to kill yeast and fungi.

BACKGROUND OF THE INVENTION

(1) Field of the Invention

During the study of limonene as a hand cleaner, the applicants found that fully oxygenated limonene is a fungicide. A reveiw of the literature revealed that oxygenated limonene contains several oxidation products including: limonene-1,2-oxide, limonene-8,9-oxide, 1-menthene-9-al, α-2,8-p-menthadiene-1-ol, β-2,8p-menthadiene-1-ol, dihydrocarvone, β-cymenol, carvone, cis-carveol, and trans-carveol, as :;as outlined by Bain in U.S. Pat. Nos 2,863,882 and 3,014,047. Blumann listed the compounds formed by the auto-oxidation of limonene in Chemical Abstracts, Volume 63, 1965, on page 1819, which included cis-carveol, trans-carveol, trans-p-menth-8-ene-1,2-diol, limonene 1,2-epoxide, limonene 8,9-epoxide, cis and trans-p-mentha-2,8-dien-1-01, and perillyl alcohol. Even though it was unexpected, the applicants found that effecitve concentrations of dihydrocarvone kills yeast and fungicidal concentrations of dihydrocarvone kills fungi.

Dihydrocarvone is a monocyclic monoterpene with the following chemical formula: ##STR1##

Dihydrocarvone is an oil with a terpenic aroma. It is insoluble in water and glycerine. Dihydrocarvone is soluble in alcohol and is miscible in corn oil, olive oil, and soybean oil, etc. Dihydrocarvone has been used as a bactericide, but heretofore, it has never been demonstrated to kill yeast or fungi.

Bain in U.S. Pat. No. 2,803,647 showed his method of producing carveol and dihydrocarvone and their esters.

(2) Description of the Prior Art

Zukerman studied the effect of auto-oxidized limonene on bacteria. He found it was weakly bacteriostatic, was unstable, and that it lost its bacteriostatic effect on keeping as was discussed in Nature 168: 517 (1951). He never studied oxidized limonene nor dihydrocarvone for fungicidal activity. Kurita investigated the fungicidal activity of several components of essential oils in Biol. Chem., 45(4), 945-952, 1981, and noted that cineole, anethole, safrole, d-limonene, α-pinene, β-pinene, camphene, β-myrcene, caryophyllene, β-cymene, d-camphor, benzaldehyde, vanillin, and furfural are not fungicidal while cinnamaldehyde, phenol, perillyl aldehyde, citral, perillyl alcohol, geraniol, citronellol, 1-nonanol, 1-decanol 1-menthol and borneol have minimal to good fungicidal activity. He never studied the anti-yeast or anti-fungal activity of dihydrocarvone. Peter Tetenyi et al studied essential oils obtained from twelve different specimens of Tanacetum vulgare L. and found eight of the twelve specimens to be bactericidal in a concentration of 100 ug/ml against 85-90% of nineteen different bacteria and 100% fungicidal against sixteen species of fungi in a concentration of 50 ug/ml. He delineated numerous chemical components in the oils but he never studied dihydrocarvone or any of the individual components in the oils for anti-bacterial, anti-yeast and/or anti-fungal activity as was outlined in Herba Hungarica, 1981, Tom 20, No. 1-2, pages 57-74. In Botanical Gazette 122, 194-8 (1961), R. C. French showed that carveol and dihydrocarveol stimulate the germination of wheat stem rust uredospores suggesting that carveol and dihydrocarveol promote the growth of fungi. J. C. Maruzzella and L. Liguori reported the in vitro anti-fungal activity of essential oils in the Journal of the American Pharmaceutical Association, Vol. XLVII, No. 4, April 1958, pages 250-4, but they did not study the fungicidal activity of dihydrocarvone. J. C. Maruzzella and Jerry Balter showed the action of essential oils on phytopathogenic fungi in the Plant Disease Reporter Vol. 43, No. 11, Nov. 1959, pages 1143-1147, but they did not study the anti-yeast or the anti-fungal activity of dihydrocarvone. Gauvreau showed a means of producing disinfecting compositions in U.S. Pat. No. 3,595,975 by combining cetyl pyridinium with terpenes to form antiseptics. Gauvreau never studied the use of dihydrocarvone alone nor in combination with cetyl pyridinium. Chastain and Sanders discovered a method of making limonene bactericidal and fungicidal as described in U.S. Pat. No. 5,153,229, but they never studied dihydrocarvone for

bactericidal nor fungicidal activity. A. Morel revealed the sterilizing action of carveol, dihydrocarveol, and their ozonization products in Comp. Rend. Soc. Biol. Volume 115, pages 536-8 (1934). He demonstrated the bactericidal activity of carveol and dihydrocarveol but he never studied their anti-yeast or anti-fungal activity. D. D. Whitehead in U.S. Pat. No. 3,743,747 showed the fungicidal activity of several oxo-derivatives of limonene and dipentene, but he never studied the anti-yeast or anti-fungal activity of dihydrocarvone. J. C. Maruzzella et al reported the action of odoriferous organic chemicals and essential oils on wood-destroying fungi in the Plant Disease Reporter Vol 44, No. 10 (1960); dihydrocarvone was never studied. Murdock and Allen showed the germicidal effect of sodium benzoate against yeast is enhanced by orange peel oil and d-limonene (stripper oil), as was reported in Food Technology, Vol 14, No. 9, 1960, pages 441-5. They never studied the action of dihydrocarvone against yeast or fungi. Kellner et al studied ethereal oils for antimicrobial activity, but they never studied the oils nor any of their chemical constituents for anti-yeast or anti-fungal activity as was outlined in Arzneimittel-Forschung 5 224-9 (1955).

It should be pointed out that the drugs which are bactericidal are usually not fungicidal, and drugs which are fungicidal are usually not bactericidal. In humans, the use of bactericidal antibiotics frequently promotes the growth of yeast. Table A, which follows, exemplifies the anti-bacterial, anti-yeast and anti-fungal activity of several commonly used anti-bacterial, anti-yeast, and anti-fungal antibiotics.

                                      TABLE A                                      __________________________________________________________________________                 ANTIBIOTIC ACTIVITY AGAINST                                        ANTIBIOTICS Gm + Bact                                                                             Gm - Bact                                                                             A F Bact                                                                            Yeast                                                                              Fungi                                       __________________________________________________________________________     A. ANTIBACTERIAL                                                               1. Ampicillin                                                                              YES    YES    NO   NO  NO                                          2. Cephalothin                                                                             YES    YES    NO   NO  NO                                          3. Chloramphenicol                                                                         YES    YES    NO   NO  NO                                          4. Erythromycin                                                                            YES    NO     NO   NO  NO                                          5. Ethambutol                                                                              NO     NO     YES  NO  NO                                          6. Gentamicin                                                                              YES    YES    NO   NO  NO                                          7. Isoniazid                                                                               NO     NO     YES  NO  NO                                          8. Nitrofurantoin                                                                          NO     YES    NO   NO  NO                                          9. Penicillin                                                                              YES    NO     NO   NO  NO                                          10. Rifampin                                                                               YES    NO     YES  NO  NO                                          11. Streptomycin                                                                           YES    YES    YES  NO  NO                                          12. Sulfonamides                                                                           NO     YES    NO   NO  NO                                          13. Tetracycline                                                                           YES    YES    NO   NO  NO                                          14. Vancomycin                                                                             YES    YES    NO   NO  NO                                          B. ANTIYEAST                                                                   1. Nystatin NO     NO     NO   YES NO                                          2. Gentian Violet                                                                          NO     NO     NO   YES NO                                          C. ANTIFUNGAL                                                                  1. Chlotrimazole                                                                           NO     NO     NO   YES YES                                         2. Griseofulvin                                                                            NO     NO     NO   NO  YES                                         __________________________________________________________________________      Gm + Bact = Gram Positive Bacteria, Gm - Bact = Gram Negative Bacteria, A      F Bact =  Acid Fast Bacteria, YES = Kills Organism, NO = No Activity           Against Organism                                                         

It should be noted in the table above that none of the anti-bacterial antibiotics kill yeast nor fungi, and none of the anti-yeast nor anti-fungal antibiotics kill bacteria. Thus an anti-fungal or anti-yeast antibiotic is not expected to kill bacteria, and an anti-bacterial antibiotic is not expected to kill yeast or fungi. Anti-fungal antibiotics do not necessarily kill yeast, and anti-yeast antibiotics do not necessarily kill fungi.

Several differences between yeast and fungi are known and are listed. For instance: (1) yeast can be grown in a culture in 24-48 hours while a fungus requires 7-14 days to grow in a culture. (2) Yeast grow on blood agar while fungi grow on sabouraud dextrose agar. (3) The use of anti-bacterial antibiotics in humans promotes the grow of yeast but the use of anti-bacterial antibiotics in humans does not promote the growth of fungi. (4) Several anti-yeast antibiotics do not kill fungi and several anti-fungal antibiotics do not kill yeast.

DISCLOSURE OF THE INVENTION

This invention relates to the use of dihydrocarvone to kill yeast and fungi. Dihydrocarvone is an oil which is available commercially, but heretofore, it has not been shown to kill yeast or fungi. It is slightly viscous, and when applied, readily adheres to glass, metal, wood, cloth, rope, book covers, paper, cement, ceramics, paint, plastic, plant surfaces, skin, mucus membranes, and teeth leaving an oily film. Because it is not soluble in water its adherence to surfaces allows prolonged exposure and makes dihydrocarvone ideal for treating yeast and fungus infections of plants, animals, and humans.

The exact method of killing yeast and fungi is unknown, but it is thought that dihydrocarvone kills yeast and fungi by lysing the cell membrane of the organism which is lethal to the organism.

In practice, any surface, on which it is desirable to kill or prevent the growth of yeast or fungi, is treated with effective concentrations of dihydrocarvone to kill yeast, or fungicidal concentrations of dihydrocarvone to kill fungi by swabbing, wiping, painting, washing, brushing, spraying, or any other direct application technique. Alternatively, dihydrocarvone can be incorporated in creams, ointments, tinctures, gels, suppositories, paints, sprays, aerosols, toothpastes, solutions, emulsions, soaps, scrubs, mouthwashes, or antiseptics and applied anywhere it is desirable to kill or prevent the growth of yeast or fungi.

BEST MODE FOR CARRYING OUT THE INVENTION

The following examples are illustrative of the best mode for carrying out the invention. They are, obviously, not to be construed as limitative of the invention since various other embodiments can readily be evolved in view of the teachings provided herein.

EXAMPLE 1 Anti-Yeast And Anti-Fungal Activity of Dihydrocarvone

The anti-yeast and anti-fungal compound contemplated by this invention is dihydrocarvone which was studied for anti-yeast and anti-fungal activity. The organisms tested included the yeast, Candida albicans, that causes infections of skin and mucus membranes; the cutaneous fungus, Microsporum canis, that infects man and animals, and the mildew causing fungi Aureobasidium pullulans OM 279C, Cladosporium cladosporiodes OM 489, and Phialophora lignicola OM 5922. The minimal effective concentration of dihydrocarvone needed to kill yeast and the fungicidal concentration needed to kill fungi are listed in Table B below. The dihydrocarvone used in the tests were obtained from Aldrich Chemical Company, Milwaukee, Wis. The Catalogue Number and Lot Number for the dihydrocarvone were 21,842-1 and TD092197 respectively.

                  TABLE B                                                          ______________________________________                                         ANTI-YEAST AND ANTI-FUNGAL                                                     ACTIVITY OF dl DIHYDROCARVONE                                                  ______________________________________                                         ORGANISM         MINIMUM EFFECTIVE                                                              CONCENTRATION                                                 A. YEAST         10 MIN   60 MIN   24 HOURS                                    1. Candida albicans                                                                              >0.016   0.016   0.005                                       B. FUNGI         MINIMUM FUNGICIDAL                                                             CONCENTRATION                                                 1. Microsporum canis                                                                            >0.16    >0.16    0.0012                                      2. Aureobasidium pullulans                                                                      >0.16    0.06     0.0012                                      Om 279C                                                                        6. Cladoscorium cladosporiodes                                                                  >0.16    0.16     0.0012                                      OM 489                                                                         7. Phialophora lignicola                                                                         0.16    0.10     0.0012                                      OM 5922                                                                        ______________________________________                                    

The standard assay used to test the activity of dihydrocarvone against yeast and fungi was as follows: various dilutions of dihydrocarvone were individually prepared in Sabouraud dextrose broth medium. An inoculum of 10⁶ colony-forming units (CFU/ml) of yeast or fungi were introduced into each test, after which it was incubated at 37° C. in air, and subcultured (0.01 ml) at 10 minutes, 60 minutes, and 24 hours onto agar media free of dihydrocarvone. Results were expressed as the minimal lethal concentration, i.e. the lowest concentration of dihydrocarvone (ml dihydrocarvone/total ml of test) with no detectable viable colonies following subculture onto media free of dihydrocarvone.

Details of each assay are presented in Table C which follows.

                                      TABLE C                                      __________________________________________________________________________     Test conditions used to assay the anti-yeast and anti-fungal                   activity of dihydrocarvone                                                                        SUBCULTURE INCUBATION                                       ORGANISM                                                                               BROTH MEDIUM                                                                              AGAR MEDIUM                                                                               CONDITIONS                                       __________________________________________________________________________     1. Yeast                                                                               Sabouraud  5% sheep blood                                                                            air at 37° C.                                     Dextrose                                                               2. Fungi                                                                               Sabouraud  Sabouraud  air at 30° C.                                     Dextrose   Dextrose agar                                               __________________________________________________________________________

EXAMPLE 2 Formulations Which Include The Anti-Yeast And The Anti-Fungal Compound Dihydrocarvone

The following formulations are prepared using dihydrocarvone in liquids, gels, soaps, paints, pastes, creams, ointments, solutions, tinctures, suppositories, tampons, aerosols, and emulsions. When yeast or fungi are treated with dihydrocarvone containing formulations, the formulations kill or prevent the growth yeast or fungi.

    __________________________________________________________________________     CHEMICAL        % OF TOTAL                                                                              RANGE  ACTION                                         __________________________________________________________________________     A. LIQUIDS                                                                     1. SOLUTIONS OR SPRAYS                                                         a. Dihydrocarvone                                                                              5.0%     0.1-50%                                                                               fungicide                                      Corn Oil        95.0%    50-99.9%                                                                              diluent                                                        100.0%                                                         b. Dihydrocarvone                                                                              1.0%     0.1-50%                                                                               fungicide                                      Ethyl Alcohol   99.0%    50-99.9%                                                                              diluent                                                        100.0%                                                         2. MOUTHWASH                                                                   a. Dihydrocarvone                                                                              50.0%    0.1-50%                                                                               anti-yeast                                     Flavor          2.0%     1-5%   flavor                                         Ethyl Alcohol   48.0%    45-98.9%                                                                              diluent                                                        100.0%                                                         B. DENTIFRICE                                                                  1. LIQUID                                                                      Liquid soap concentrate                                                                        5.0%     2-10%  surfactant                                     Saccharin       0.2%     0.1-1.0%                                                                              flavor                                         Clove Oil       1.0%     0.5-3.0%                                                                              flavor                                         Cinnamon Oil    0.5%     0.5-3.0%                                                                              flavor                                         Peppermint Oil  0.5%     0.5-3.0%                                                                              flavor                                         Ethyl Alcohol   42.6%    29.5-95.3%                                                                            diluent                                        Color           0.2%     0.1-0.5%                                                                              color                                          Dihydrocarvone  50.0%    1-50%  fungicide                                                      100.0%                                                         Sodium monofluorophosphate                                                                     0.8%     0.5-1.5%                                                                              antiplaque                                     Dihydrocarvone  50.0%    1-50%  anti-yeast                                     Hydrated silica xerogel                                                                        10.0%    8-15%  abrasive                                       Hydrated thickening silica                                                                     8.5%     5-10%  binder                                         Sorbitol 70% solution                                                                          18.8%    5-73.3%                                                                               humectant                                      Polyethylene glycol 32                                                                         5.0%     3-7%   bodying                                                                        agent                                          Sodium lauryl sulfate                                                                          1.5%     1-2%   surfactant                                     Carboxymethyl cellulose                                                                        1.0%     0.5-2% binder                                         gum                                                                            S D alcohol     1.0%     0.5-2% stabilizer                                     Flavor          3.0%     2-4%   flavor                                         Saccharin       0.2%     0.1-0.5%                                                                              flavor                                         F D & C Green #3                                                                               0.1%     0.1-0.5%                                                                              color                                          F D & C Yellow #10                                                                             0.1%     0.1-0.5%                                                                              color                                                          100.0%                                                         3. PASTE                                                                       Sodium monofluorophosphate                                                                     0.8%     0.5-1.5%                                                                              antiplaque                                     Dihydrocarvone  50.0%    1-50%  fungicide                                      Dicalcium phosphate                                                                            22.0%    20.4-30%                                                                              abrasive                                       dihydrate                                                                      Water           16.0%    11.1-69.5%                                                                            diluent                                        Glycerine       5.1%     4.5-12.5%                                                                             bodying                                                                        agent                                          Flavor          2.0%     2-3%   flavor                                         Sodium lauryl sulfate                                                                          1.5%     1-2%   surfactant                                     Carboxymethyl cellulose                                                                        1.4%     0.5-2.0%                                                                              binder                                         gum                                                                            Tetrasodium pyrophosphate                                                                      1.0%     0.5-2.0%                                                                              binder                                         Sodium saccharin                                                                               0.2%     0.1-0.5%                                                                              flavor                                                         100.0%                                                         C. OINTMENTS & SUPPOSITORIES WITH                                              AND WITHOUT HYDROCORTISONE                                                     1. OINTMENT WITH                                                               HYDROCORTISONE                                                                 Dihydrocarvone  1.0%     0.1-15.0%                                                                             fungicide                                      Polyethylene glycol                                                                            59.5%    48.5-59.7%                                                                            bodying                                        3350                            agent &                                                                        emulsifier                                     Polyethylene glycol                                                                            39.5%    31.5-39.7%                                                                            bodying                                        400                             agent &                                                                        emulsifier                                     Hydrocortisone  1.0%     0.5-5.0%                                                                              anti-                                                          100.0%          inflam-                                                                        matory                                         2. OINTMENT WITHOUT                                                            HYDROCORTISONE                                                                 Dihydrocarvone  1.0%     0.1-15 0%                                                                             fungicide                                      Polyethylene glycol                                                                            59.5%    51.0-59.95%                                                                           bodying                                        3350                            agent &                                                                        emulsifier                                     Polyethylene glycol                                                                            39.5%    34.0-39.95%                                                                           bodying                                        400             100.0%          agent &                                                                        emulsifier                                     3. SUPPOSITORY WITHOUT                                                         HYDROCORTISONE                                                                 Dihydrocarvone  1.0%     0.1-15%                                                                               fungicide                                      Polyethylene glycol                                                                            9.5%     51.0-59.95%                                                                           bodying                                        1000                            agent &                                                                        emulsifier                                     Polyethylene glycol                                                                            39.5%    34.0-39.95%                                                                           bodying                                        3350            100.0%          agent &                                                                        emulsifier                                     4. SUPPOSITORY WITH                                                            HYDROCORTISONE                                                                 Dihydrocarvone  1.0%     0.1-15%                                                                               anti-yeast                                     Polyethylene glycol                                                                            74.0%    60.0-75.2%                                                                            bodying                                        1000                            agent &                                                                        emulsifier                                     Polyethylene glycol                                                                            24.0%    20.0-24.2%                                                                            bodying                                        3350                            agent &                                                                        emulsifier                                     Hydrocortisone  1.0%     0.5-5.0%                                                                              anti-                                                          100.0%          inflam-                                                                        matory                                         D. CREAM WITHOUT HYDROCORTISONE                                                1. Dihydrocarvone                                                                              1.0%     0.1-15.0%                                                                             fungicide                                      Cetyl alcohol   15.0%    12.0-18.0%                                                                            thickener                                      Arlacel 165**   5.0%     3.5-7.5%                                                                              emulsifier                                     Sorbitol 70% solution                                                                          5.0%     3.5-8.0%                                                                              humectant                                      Water           74.5%    51.5-80.9%                                                                            diluent                                                        100.0%                                                         2. Dihydrocarvone                                                                              1.0%     0.1-15.0%                                                                             fungicide                                      Spermaceti wax  12.5%    10.0-15.0%                                                                            thickener                                      Sorbitan monostearate                                                                          10.0%    7.5-12.5%                                                                             emulsifier                                     Polyethylene 20                                                                Sorbitan monostearate                                                                          6.0%     4.0-8.0%                                                                              emulsifier                                     Water           75.5%    49.5-78.4%                                                                            diluent                                                        100.0%                                                         E. CREAMS WITH HYDROCORTISONE                                                  1. Dihydrocarvone                                                                              1.0%     0.1-15.0%                                                                             fungicide                                      Cetyl alcohol   15.0%    12.0-18.0%                                                                            thickener                                      Arlaoel 165**   5.0%     3.5-7.5%                                                                              emulsifier                                     Sorbitol 70% solution                                                                          5.0%     3.5-8.0%                                                                              humectant                                      Hydrocortisone  1.0%     0.5-5.0%                                                                              anti-                                                                          inflam-                                                                        matory                                         Water           73.0%    46.5-80.4%                                                                            diluent                                                        100.0%                                                          *Croda, Inc., 51 Madison Ave., New York, New York 10010                        **Glycerol monostearate and polyoxyethylene stearate ICI of America            (Formerly Atlas Chemical Industries), Wilmington, Delaware 19899              F. TAMPONS                                                                     1. Dihydrocarvone 2 cc 2 Gm                                                                    8%       1-15%  fungicide                                      Tampon 23 Gm    92%      85-99% reservoir                                                      100.0%          for                                                                            fungicid                                       G. AEROSOLS WITHOUT HYDROCORTISONE                                             1. Dihydrocarvone                                                                              5.0%     0.5-50%                                                                               fungicide                                      Ethyl alcohol   95.0%    50-99.5%                                                                              diluent                                                        100.0%                                                         Pressurized nitrogen                                                           propellant at 100-125                                                          psig                                                                           2. Dihydrocarvone                                                                              10.0%    0.5-50.0%                                                                             fungicide                                      Soybean oil     90.0%    50.0-99.5%                                                                            diluent                                                        100.0%                                                         Pressurized nitrogen                                                           propellant at 100-125                                                          psig                                                                           H. AEROSOL WITH HYDROCORTISONE                                                 1. Dihydrocarvone                                                                              1.0%     0.5-50%                                                                               fungicide                                      Soybean oil     98.0%    45-99.0%                                                                              diluent                                        Hydrocortisone  1.0%     0.5-5.0%                                                                              anti-                                                          100.0%          inflam-                                                                        matory                                         Pressurized nitrogen                                                           propellant at 100-125                                                          psig                                                                           I. OIL IN WATER EMULSION                                                       1. Dihydrocarvone                                                                              0.1%     0.1-50%                                                                               fungicide                                      Corn oil        10.0%    10-15% oil                                            Arlacel 40**    2.0%     1-3%   emulsifier                                     Tween 40        3.0%     2-4%   emulsifier                                     2. Water        84.9%    28-86.9%                                                                              diluent                                                        100.0%                                                          Heat 1 to 70° C. Heat 2 to 72° C. Add 2 to 1 with agitation      Stir until cooled to room temperature.                                        J. OIL IN WATER EMULSION WITH SOAP (FUNGICIDAL SOAP)                           1. Dihydrocarvone                                                                              1.0%     0.1-25%                                                                               fungicide                                      Corn oil        30.0%    20.0-40.0%                                                                            oil                                            Arlacel 40**    2.0%     1.0-3.0%                                                                              emulsifier                                     Tween 40        3.0%     2.0-4.0%                                                                              emulsifier                                     Liquid soap concentrate                                                                        3.5%     2.5-5.0%                                                                              surfactant                                     2. Water        60.5%    23-74.4%                                                                              diluent                                                        100.0%                                                          Heat 1 to 70° C. Heat 2 to 72° C. Add 2 to 1. Stir until         cooled to room temperature.                                                   K. WATER IN OIL EMULSION                                                       1. Dihydrocarvone                                                                              1.0%     0.1-25%                                                                               fungicide                                      Arlacel 186**   3.0%     2.0-4.0%                                                                              emulsifier                                     Soybean oil     15.0%    10.0-25.0%                                                                            oil                                            Ceresin wax     0.5%     0.3-0.6%                                                                              thickener                                      Beeswax         0.5%     0.3-0.6%                                                                              thickener                                      Tween 80        0.5%     0.3-0.6%                                                                              emulsifier                                     2. Water        79.5%    44.2-87.0%                                                                            diluent                                                        100.0%                                                          Heat 1 to 70° C. Heat 2 to 72° C. Add 2 to 1 with continuou      agitation.                                                                    L. PAINT                                                                       1. ENAMEL                                                                      Dihydrocarvone  1.0%     1-10%  fungicide                                      Titanium dioxide                                                                               14.91%   12-16% pigment                                        Calcium carbonate                                                                              29.83%   25-35% pigment                                        Silicate        4.81%    3-6%   pigment                                        Soya alkyd resin                                                                               25.72%   22-28% pigment                                                                        (binder)                                       Mineral spirits 23.73%   5-37%  solvent                                                        100.00%         (thinner)                                      2. LATEX                                                                       Dihydrocarvone  1.0%     1-10%  fungicide                                      Titanium dioxide                                                                               10.76%   8-12%  pigment                                        Silicate        12.91%   10-16% pigment                                        Calcium carbonate                                                                              20.91%   15-25% pigment                                        Vinyl acrylic resin                                                                            12.22%   10-16% vehicle                                        solids                          (binder)                                       Glycol          8.47%    6-10%  solvent                                                                        (thinner)                                      Water           34.0%    12-50% solvent                                                        100.0%          (thinner)                                      __________________________________________________________________________

While only certain preferred embodiments of this invention have been shown and described by way of illustration, many modifications will occur to those skilled in the art and it is, therefore, desired that it be understood that it is intended herein, to cover all such modifications that fall within the true spirit and scope of this invention. 

We claim:
 1. A method of killing fungi or yeast comprising treating fungi or yeast in their habitat with toxic concentrations of dihydrocarvone.
 2. The method of claim 1 for killing fungi wherein said fungi are selected from a group consisting of Microsporum, Aureobasidium, Cladosporium, and Phialophora.
 3. The method of claim 1 for killing yeast wherein said yeast is Candida. 